One-pot diastereoselective synthesis of highly functionalized chromenone-substituted 4,5-dihydrofuran via sequential three-component reaction

Journal of the Iranian Chemical Society(2022)

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摘要
This study describes a fast and one-pot diastereoselective sequential three-component reaction (3CR) involving phenacyl bromide, malononitrile, and 4-oxo-4 H -chromene-3-carbaldehyde. This reaction could be used for the preparation of highly functionalized 2-amino-4,5-dihydrofuran-3-crabonitrile. In this procedure, the desired product is obtained through a reaction of phenacylmalononitrile (obtained from the reaction of phenacyl bromide and malononitrile) with 4-oxochromene-3-carbaldehyde. This method has benefits such as good efficiency, proper diversity, relatively short reaction time, and simple product purification. Graphical abstract A series of highly functionalized 2-amino-4,5-dihydrofuran-3-crabonitrile frameworks have been synthesized in excellent yields (80–85%) via a one-pot three-component reaction of phenacyl bromide, malononitrile, and 4-oxo-4 H -chromene-3-carbaldehyde, in good yield. The value of this method lies in its short reaction time, convenient purification, no need for a metal catalyst, good efficiency, and green solvent.
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关键词
2-Amino-4,5-dihydrofuran-3-crabonitrile,4-Oxo-4H-chromene-3-carbaldehyde,Malononitrile,Multicomponent reaction,Phenacyl bromide
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